US6589903B2 - Method of synthesizing complexes of platinum and alkenylpolysiloxane, especially of platinum and divinyltetramethyldisiloxane - Google Patents
Method of synthesizing complexes of platinum and alkenylpolysiloxane, especially of platinum and divinyltetramethyldisiloxane Download PDFInfo
- Publication number
- US6589903B2 US6589903B2 US09/910,494 US91049401A US6589903B2 US 6589903 B2 US6589903 B2 US 6589903B2 US 91049401 A US91049401 A US 91049401A US 6589903 B2 US6589903 B2 US 6589903B2
- Authority
- US
- United States
- Prior art keywords
- platinum
- suspension
- alkenylpolysiloxane
- liquid phase
- activated charcoal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 title claims abstract description 35
- 229910052697 platinum Inorganic materials 0.000 title claims abstract description 35
- FSIJKGMIQTVTNP-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C=C)C=C FSIJKGMIQTVTNP-UHFFFAOYSA-N 0.000 title claims description 4
- 230000002194 synthesizing effect Effects 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 12
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 239000007791 liquid phase Substances 0.000 claims description 25
- 239000000725 suspension Substances 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical compound [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 claims description 8
- 239000003791 organic solvent mixture Substances 0.000 claims description 7
- 239000011877 solvent mixture Substances 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000003057 platinum Chemical class 0.000 claims description 3
- 239000007790 solid phase Substances 0.000 claims 6
- 239000007788 liquid Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000002245 particle Substances 0.000 description 5
- 229910002621 H2PtCl6 Inorganic materials 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- -1 platinum siloxane Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006459 hydrosilylation reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- HRVYEARUCOSYME-UHFFFAOYSA-N [bis(ethenyl)-phenylsilyl]oxy-dimethyl-phenylsilane Chemical compound C=1C=CC=CC=1[Si](C)(C)O[Si](C=C)(C=C)C1=CC=CC=C1 HRVYEARUCOSYME-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- POPWUTFDMIFIRN-UHFFFAOYSA-N bis(ethenyl)-bis(trimethylsilyloxy)silane Chemical compound C[Si](C)(C)O[Si](C=C)(C=C)O[Si](C)(C)C POPWUTFDMIFIRN-UHFFFAOYSA-N 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1608—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes the ligands containing silicon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2291—Olefins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0086—Platinum compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/398—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing boron or metal atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/828—Platinum
Definitions
- the invention relates to a method for the synthesis of complexes of platinum and alkenylpolysiloxane, and especially to platinum divinyltetramethyldisiloxane, which is synthesized by this method, and to several uses.
- a method for the synthesis of a platinum hydrosilylation catalyst for which initially a mixture of a haloplatinic acid, an alkenylpolysiloxane and a cycloalkylpolysiloxane is stirred at a particular temperature, after which the essentially the halogen is removed with sufficient alkali and the mixture is filtered, in order to obtain the corresponding platinum hydrosilylation catalyst.
- a mixture of a haloplatinic acid, an alkenylpolysiloxane and a cycloalkylpolysiloxane is stirred at a particular temperature, after which the essentially the halogen is removed with sufficient alkali and the mixture is filtered, in order to obtain the corresponding platinum hydrosilylation catalyst.
- 0.3 to about 20 moles of cycloalkylpolysiloxane per mole of alkenylpolysiloxane must be made available.
- a haloplatinum compound is reacted with at least one alkenylpolysiloxane with the addition of platinum in the form of a platinum complex as autocatalyst and with the addition of at least one base, especially of a hydrogen carbonate, carbonate or hydroxide, at the lowest possible temperature, especially at a temperature below +60° C., in an organic solvent mixture or solvent mixture, which can be oxidized by the haloplatinum compound.
- reaction formulation is stirred during the reaction, for example, by means of a magnetic stirrer, for better mixing and in order to avoid local overheating.
- the individual reactants are added to the reaction formulation, for example, in portions or dropwise.
- activated charcoal is added before the reaction.
- the activated charcoal suspension obtained is concentrated and, subsequently, the solid particles and activated charcoal are separated from a first liquid phase, preferably by filtration, or the solid particles and activated charcoal are separated from a first liquid phase and, subsequently, the first liquid phase is concentrated.
- the reaction product, a platinum alkenylpolysiloxane is contained in the liquid phase.
- the solid particles are separated from a first liquid phase after the reaction. Subsequently, the first liquid phase is treated with activated charcoal to form an activated charcoal suspension. After that, the suspension is concentrated and the activated charcoal is separated from the first liquid phase or the activated charcoal is separated from the first liquid phase and, subsequently, the first liquid phase is concentrated.
- the reaction suspension obtained after the reaction is treated with activated charcoal to form an activated charcoal suspension.
- the activated charcoal suspension is concentrated, whereupon the solid particles and the activated charcoal are separated from a first liquid phase or the solid particles and activated charcoal are separated from a first liquid phase and, subsequently, the first liquid phase is concentrated.
- the alkenylpolysiloxane is added first to the solvent or solvent mixture. This is followed by the addition of the haloplatinum compound. If the addition is reversed, unstable solutions may be formed, which may still react even days after they are formed.
- divinyltetramethyldisiloxane has proven its value in practice as alkenylpolysiloxane and hexachloroplatinic acid has proven its value in practice as haloplatinum compound.
- At least one alcohol especially isopropanol and/or ethanol as solvent or solvent mixture.
- haloplatinum compound is added as an anhydrous solution to the reaction formulation, especially as a solution of the haloplatinum compound in isopropanol, a controlled evolution of carbon dioxide gas takes place advantageously which, in turn, limits the discharge of the solvent by gas evolution, so that it is also possible to adhere to the strict emission limits.
- the alkenylpolysiloxane, especially the platinum divinyltetramethyldisiloxane, synthesized with this method, is almost colorless in comparison with the substances synthesized by methods known from the state of the art and has an iodine color number of 0 to 15 (measured according to DIN 6162).
- reaction temperature can be lowered by up to about 20° K in this way, as a result of which fewer decomposition products and byproducts are formed and the reaction product is less contaminated.
- the synthesis is carried out under an inert gas.
- Sodium hydrogen carbonate (42 g) is added to the apparatus and suspended in 62 ml of divinyltetramethyldisiloxane, 1 g of platinum siloxane con complex and 150 ml of isopropanol. The suspension is heated with stirring to a temperature of +48° C. to +52° C. and kept at this temperature.
- a solution of 10 g of platinum as H 2 PtCl 6 solid in 25 ml of isopropanol is prepared. Subsequently, the solution is run into the suspension in 5 ml steps, each subsequent addition being made after the suspension has decolorized once again. The temperature is maintained between +48° C. and +53° C.
- the reaction is exothermic and a strong evolution of gas may be observed.
- the suspension is stirred for at least a further 2 hours, until it has decolorized.
- the suspension formed is cooled with stirring to room temperature and subsequently filtered through a G3 sintered glass disk. The filter cake is washed with 75 ml of isopropanol.
- solution 1 is treated with 6 g of activated charcoal and concentrated in a rotary evaporator under vacuum at a temperature not exceeding +45° C. (up to a platinum concentration of about 20%), until no further distillate is formed.
- the solution is then filtered through a Blauband filter.
- the activated charcoal is washed with 200 ml of isopropanol and added to “solution 1” for the next experiment.
- the synthesis is carried out under an inert gas.
- the synthesis is carried out under an inert gas.
- the synthesis is carried out under an inert gas.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10035644.3 | 2000-07-20 | ||
| DE10035644A DE10035644C1 (de) | 2000-07-20 | 2000-07-20 | Verfahren zur Herstellung von Platin-Alkenylpolysiloxan-Komplexen, insbesondere von Platin-Divinyltetramethyldisiloxan |
| DE10035644 | 2000-07-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| US20020099159A1 US20020099159A1 (en) | 2002-07-25 |
| US6589903B2 true US6589903B2 (en) | 2003-07-08 |
Family
ID=7649799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US09/910,494 Expired - Lifetime US6589903B2 (en) | 2000-07-20 | 2001-07-19 | Method of synthesizing complexes of platinum and alkenylpolysiloxane, especially of platinum and divinyltetramethyldisiloxane |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US6589903B2 (de) |
| EP (1) | EP1174435B1 (de) |
| JP (1) | JP3842591B2 (de) |
| DE (2) | DE10035644C1 (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030073859A1 (en) * | 2001-10-16 | 2003-04-17 | W.C. Heraeus Gmbh & Co. Kg | Process for producing platinum alkenyl polysiloxane complex compounds, especially platinum divinyltetramethyldisiloxane |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE316545T1 (de) * | 2003-10-04 | 2006-02-15 | Goldschmidt Gmbh | Verfahren zur herstellung von organischen siliciumverbindungen |
| CA3061805A1 (en) | 2017-06-27 | 2019-01-03 | Heraeus Deutschland GmbH & Co. KG | Synergistic combinations of platinum and rhodium compounds as catalysts in hydrosilylation |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3715334A (en) | 1970-11-27 | 1973-02-06 | Gen Electric | Platinum-vinylsiloxanes |
| US5098980A (en) | 1989-08-31 | 1992-03-24 | Dow Corning Toray Silicone Company, Ltd. | Platinum catalyst composition, method for its preparation and curable organopolysiloxane compositions containing same |
| US5175325A (en) * | 1991-02-14 | 1992-12-29 | Dow Corning Limited | Platinum complexes and use thereof |
| EP0894804A2 (de) | 1997-07-28 | 1999-02-03 | Dow Corning Toray Silicone Company, Ltd. | Platinumkomplex haltende katalytische Zusammensetzung, Verfahren für seine Herstellung und katalytische Zusammensetzung aus einem thermoplastischen Harzmikropartikel |
| EP0979837A2 (de) | 1998-08-13 | 2000-02-16 | General Electric Company | Verfahren zur Herstellung von einem Platinhydrosilylierungs-Katalysator |
-
2000
- 2000-07-20 DE DE10035644A patent/DE10035644C1/de not_active Expired - Fee Related
-
2001
- 2001-06-15 EP EP01114495A patent/EP1174435B1/de not_active Expired - Lifetime
- 2001-06-15 DE DE50107958T patent/DE50107958D1/de not_active Expired - Lifetime
- 2001-07-17 JP JP2001217198A patent/JP3842591B2/ja not_active Expired - Lifetime
- 2001-07-19 US US09/910,494 patent/US6589903B2/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3715334A (en) | 1970-11-27 | 1973-02-06 | Gen Electric | Platinum-vinylsiloxanes |
| US5098980A (en) | 1989-08-31 | 1992-03-24 | Dow Corning Toray Silicone Company, Ltd. | Platinum catalyst composition, method for its preparation and curable organopolysiloxane compositions containing same |
| US5175325A (en) * | 1991-02-14 | 1992-12-29 | Dow Corning Limited | Platinum complexes and use thereof |
| EP0894804A2 (de) | 1997-07-28 | 1999-02-03 | Dow Corning Toray Silicone Company, Ltd. | Platinumkomplex haltende katalytische Zusammensetzung, Verfahren für seine Herstellung und katalytische Zusammensetzung aus einem thermoplastischen Harzmikropartikel |
| EP0979837A2 (de) | 1998-08-13 | 2000-02-16 | General Electric Company | Verfahren zur Herstellung von einem Platinhydrosilylierungs-Katalysator |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030073859A1 (en) * | 2001-10-16 | 2003-04-17 | W.C. Heraeus Gmbh & Co. Kg | Process for producing platinum alkenyl polysiloxane complex compounds, especially platinum divinyltetramethyldisiloxane |
| US6777566B2 (en) * | 2001-10-16 | 2004-08-17 | W. C. Heraeus Gmbh & Co. Kg | Process for producing platinum alkenyl polysiloxane complex compounds, especially platinum divinyltetramethyldisiloxane |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1174435A2 (de) | 2002-01-23 |
| US20020099159A1 (en) | 2002-07-25 |
| EP1174435A3 (de) | 2003-09-03 |
| EP1174435B1 (de) | 2005-11-09 |
| JP2002053585A (ja) | 2002-02-19 |
| DE50107958D1 (de) | 2005-12-15 |
| DE10035644C1 (de) | 2001-12-20 |
| JP3842591B2 (ja) | 2006-11-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5262558A (en) | Method of making organo-silicon polymers having mono- and tetra-functional siloxane units | |
| MX2007002453A (es) | Preparacion de complejos de platino (ii). | |
| CN110776528A (zh) | 磺酸铵两性离子硅烷偶联剂、硅氧烷环体及其制备方法 | |
| US6589903B2 (en) | Method of synthesizing complexes of platinum and alkenylpolysiloxane, especially of platinum and divinyltetramethyldisiloxane | |
| JPS62198641A (ja) | カルボン酸塩の製造法 | |
| US6777566B2 (en) | Process for producing platinum alkenyl polysiloxane complex compounds, especially platinum divinyltetramethyldisiloxane | |
| IL139528A (en) | Platinum bracelets, processes for their preparation and pharmaceutical preparations containing them | |
| KR100536791B1 (ko) | 루테늄(ⅲ)아세테이트용액의제조방법 | |
| JPS5945666B2 (ja) | アミノカルボン酸類の製造方法 | |
| JP2010524870A (ja) | パラジウム（０）−ジベンジリデンアセトン錯体 | |
| JPS62198649A (ja) | カルボン酸塩の製造法 | |
| KR100379637B1 (ko) | 고순도, 고수율의 2-아미노-3,5-디브로모벤즈알데히드의제조방법 | |
| JP3878966B2 (ja) | サマリウム錯体 | |
| JP2724901B2 (ja) | メチルフェニルトリシロキサン類の製造方法 | |
| CN113173949A (zh) | 以二苯基叔丁基膦为底物合成三取代芳基氧膦物种的方法 | |
| JP4825969B2 (ja) | 第３級アルコールの製造方法 | |
| EP0324665A1 (de) | Wasserfreier Cerium(III)nitrat-Ammoniumnitrat-Komplex und Verfahren zur Herstellung, ausgehend von Cerium(IV)ammoniumnitrat | |
| JPH07267973A (ja) | 白金錯体の製造方法 | |
| JP2003190806A (ja) | アルキン二量化触媒 | |
| JPH0952718A (ja) | テトラアンミン白金（ｉｉ）ジクロライドの製造方法 | |
| JPH01308836A (ja) | テトラアンミン白金（２）クロライドの製造方法 | |
| JPH08319273A (ja) | Ｎ−置換インドール誘導体の製造方法 | |
| JPH0977755A (ja) | 新規エポキシ化剤 | |
| JPS6393775A (ja) | ４−アミノ−２（５ｈ）−フラノン誘導体の製造法 | |
| JPH08165277A (ja) | インドールまたはインドール誘導体製造用触媒の調製方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: W.C. HERAEUS GMBH & CO. KG, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:REITZ, RAMONA;WALTER, RICHARD, DR.;REEL/FRAME:012256/0377;SIGNING DATES FROM 20010810 TO 20010813 |
|
| FEPP | Fee payment procedure |
Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY |
|
| STCF | Information on status: patent grant |
Free format text: PATENTED CASE |
|
| FPAY | Fee payment |
Year of fee payment: 4 |
|
| FPAY | Fee payment |
Year of fee payment: 8 |
|
| AS | Assignment |
Owner name: HERAEUS PRECIOUS METALS GMBH & CO. KG, GERMANY Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:W.C. HERAEUS GMBH & CO. KG;REEL/FRAME:032973/0477 Effective date: 20110801 |
|
| FPAY | Fee payment |
Year of fee payment: 12 |
|
| AS | Assignment |
Owner name: HERAEUS DEUTSCHLAND GMBH & CO. KG, GERMANY Free format text: CHANGE OF NAME;ASSIGNOR:HERAEUS PRECIOUS METALS GMBH & CO. KG;REEL/FRAME:037056/0430 Effective date: 20150424 |